A-867744 - Moligand™, ≥98% , Channel blocker of nicotinic acetylcholine receptor α3 subunit;Channel blocker of nicotinic acetylcholine receptor α4 subunit;Allosteric modulator of nicotinic acetylcholine receptor α7 subunit, CAS No.1000279-69-5, Channel blocker of nicotinic acetylcholine receptor α3 subunit;Channel blocker of nicotinic acetylcholine receptor α4 subunit;Allosteric modulator of nicotinic acetylcholine receptor α7 subunit

CAS: 1000279-69-5 Cat. No.: A127582 Molecular Weight: 402.89

GRADE & PURITY Moligand™, ≥98%

Synonyms

4-(5-(4-chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide | 4-(5-(4-Chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)-benzenesulfonamide | GTPL3986 | Benzenesulfonamide, 4-(5-(4-chlorophenyl)-2-methyl-3-(1-oxopropyl)-1H-pyrrol-1-yl)- |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A-867744 is a positive allosteric modulator of α7 nAChRs (IC50 values are 0.98 and 1.12 μM for human and rat α7 receptor ACh-evoked currents respectively, in X. laevis oocytes). Displays no activity at 5-HT3A, α3β4 or α4β2 nAChRs.

Specifications

Synonyms

4-(5-(4-chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide | 4-(5-(4-Chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)-benzenesulfonamide | GTPL3986 | Benzenesulfonamide, 4-(5-(4-chlorophenyl)-2-methyl-3-(1-oxopropyl)-1H-pyrrol-1-yl)- |

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Positive allosteric modulator ofα7 nAChRs (IC50values are 0.98 and 1.12μM for human and ratα7 receptor ACh-evoked currents respectively, inX. laevisoocytes). Displays no activity at 5-HT3A, α3β4 orα4β2 nAChRs. Brain penetrant.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ALLOSTERIC MODULATOR, CHANNEL BLOCKER

Mechanism of action

Channel blocker of nicotinic acetylcholine receptor α3 subunit;Channel blocker of nicotinic acetylcholine receptor α4 subunit;Allosteric modulator of nicotinic acetylcholine receptor α7 subunit

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCC(=O)C1=C(N(C(=C1)C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)S(=O)(=O)N)C
• IUPAC Name: 4-[5-(4-chlorophenyl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide
• InChIKey: ABACVOXFUHDKNZ-UHFFFAOYSA-N
• INCHI: 1S/C20H19ClN2O3S/c1-3-20(24)18-12-19(14-4-6-15(21)7-5-14)23(13(18)2)16-8-10-17(11-9-16)27(22,25)26/h4-12H,3H2,1-2H3,(H2,22,25,26)
• Isomeric SMILES: CCC(=O)C1=C(N(C(=C1)C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)S(=O)(=O)N)C
• Molecular Weight: 402.89
• Reaxy-Rn: 11835388
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11835388&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrroles
      • Subclass Substituted pyrroles
        • Level5 Phenylpyrroles
          • Level6 Diphenylpyrroles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrroles
• Subclass: Substituted pyrroles
• Intermediate Tree Nodes: Phenylpyrroles
• Direct Parent: Diphenylpyrroles
• Alternative Parents: Benzenesulfonamides Benzenesulfonyl compounds Aryl alkyl ketones Chlorobenzenes Organosulfonamides Aryl chlorides Vinylogous amides Heteroaromatic compounds Aminosulfonyl compounds Azacyclic compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 1,2-diphenylpyrrole - Benzenesulfonamide - Benzenesulfonyl group - Aryl alkyl ketone - Aryl ketone - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Organosulfonic acid amide - Heteroaromatic compound - Vinylogous amide - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Aminosulfonyl compound - Sulfonyl - Ketone - Azacycle - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CHRNA7 Tchem Neuronal acetylcholine receptor subunit alpha-7 (4 Activities)

Discover Target: CHRNA7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRNA3 Tclin Neuronal acetylcholine receptor subunit alpha-3 (0 Activities)

Discover Target: CHRNA3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRNA4 Tclin Neuronal acetylcholine receptor subunit alpha-4 (0 Activities)

Discover Target: CHRNA4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNA7 Tchem Neuronal acetylcholine receptor protein alpha-7 subunit (3524 Activities)

Discover Target: CHRNA7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver microsomes (16955 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNB2 Tclin Neuronal acetylcholine receptor; alpha4/beta2 (3972 Activities)

Discover Target: CHRNB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Canis familiaris (36305 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rhesus monkey (3147 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Brain (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Chrna3 Neuronal acetylcholine receptor; alpha3/beta4 (1368 Activities)

Discover Target: Chrna3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 40.29, Max Conc. mM: 100; Solvent:ethanol, Max Conc. mg/mL: 4.03, Max Conc. mM: 10 with gentle warming
• Molecular Weight: 402.900 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 402.08 Da
• Monoisotopic Mass: 402.08 Da
• Topological Polar Surface Area: 90.500 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 620.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1